Advertisement

Russian Journal of General Chemistry

, Volume 75, Issue 7, pp 1045–1049 | Cite as

Reaction of (2-Nitro- and 2-Bromo-2-nitroethenyl)phosphonates with 1,3-Cyclohexadiene

  • N. A. Anisimova
  • A. A. Kuzhaeva
  • G. A. Berkova
  • L. I. Deiko
  • V. M. Berestovitskaya
Article

Abstract

Specific features of the reactions of bis(chloroethyl) 2-nitro- and 2-bromo-2-nitroethenylphosphonates with 1,3-cyclohexadiene were studied. It was found that the reaction with 2-nitroethenylphosphonate occurs stereoselectively and provides bis(2-chloroethyl) endo-(3-nitrobicyclo[2.2.2]oct-5-en-2-yl)phosphonate. 2-Bromo-2-nitroethenylphosphonate under the same conditions gives a mixture of the endo and exo isomers of the corresponding nitrobicyclooctenes. Enhanced tendency of adducts derived from gem-bromonitroethenyl-phosphonates for intramolecular transformations, such as dehydrohalogenation and aromatization, under the cycloaddition conditions was revealed.

Keywords

Adduct Phosphonate Aromatization Intramolecular Transformation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1.
    Berestovitskaya, V.M., Anisimova, N.A., Litvinov, I.A., Kuzhaeva, A.A., Berkova, G.A., Gubaidullin, A.T., and Deiko, L.I., Zh. Obshch. Khim., 2004, vol. 74, no.4, p. 575.Google Scholar
  2. 2.
    Kuzhaeva, A.A., Anisimova, N.A., Deiko, L.I., Berkova, G.A., and Berestovitskaya, V.M., Khim. Geterotsikl. Soedin., 2003, no. 8, p. 1264.Google Scholar
  3. 3.
    Kuzhaeva, A.A., Berestovitskaya, V.M., Deiko, L.I., Anisimova, N.A., and Berkova G.A., Zh. Obshch. Khim., 2002, vol. 72, no.10, p. 1752.Google Scholar
  4. 4.
    Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes (Conjugated Nitro Compounds), London: Wiley, 1994.Google Scholar
  5. 5.
    Ono, N., The Nitro Group in Organic Synthesis. Organic Nitro Chem. Ser., New York: VCH, 2001.Google Scholar
  6. 6.
    Michael, I., Blom, N., and Glintenkamp, L., J. Chem. Soc., Perkin Trans. 1, 1991, no. 8, p. 855.Google Scholar
  7. 7.
    Ono, N., Kamimura, A., and Kaji, A., J. Org. Chem., 1988, vol. 53, no.2, p. 258.CrossRefGoogle Scholar
  8. 8.
    Emel’yanov, N.P., Azanovskaya, M.M., Romanovskaya, A.P., and Kudryashova, N.D., Dokl. Akad. Nauk BSSR, 1965, vol. 9, no.2, p. 97.Google Scholar
  9. 9.
    Allen, C.F. and Bell, A., J. Am. Chem. Soc., 1939, vol. 61, p. 521.CrossRefGoogle Scholar
  10. 10.
    Alder, K. and Riekert, H., Justus Liebigs Ann. Chem., 1936, vol. 524, p. 180.Google Scholar
  11. 11.
    Petrzilka, M. and Grayson, J.I., Synthesis, 1981, no. 10, p. 753.Google Scholar
  12. 12.
    Gareev, R.D., Loginova, G.M., Zykov, I.N., and Pudovik, A.N., Zh. Obshch. Khim., 1979, vol. 49, no.1, p. 25.Google Scholar
  13. 13.
    Posner, G.N., Vinander, V., and Afarinkia, K., J. Org. Chem., 1922, vol. 57, no.15, p. 4088.CrossRefGoogle Scholar
  14. 14.
    Wolinsky, J. and Login, R., J. Org. Chem., 1992, vol. 57, no.15, p. 4088.CrossRefGoogle Scholar
  15. 15.
    Ionin, B.I. and Timofeeva, T.N., Usp. Khim., 1972, vol. 41, no.4, p. 758.Google Scholar
  16. 16.
    Gunther, H., NMR Spectroscopy: An Introduction, Chichester: Wiley, 1980.Google Scholar
  17. 17.
    Fraser, R.F., Can. J. Chem., 1962, vol. 40, p. 78.Google Scholar
  18. 18.
    Kas’yan, A.O., Krasnovskaya, O.Yu., Zlenko, E.T., Okovityi, S.I., and Kas’yan, M.I., Zh. Org. Khim., 1996, vol. 32, no.8, p. 1156.Google Scholar
  19. 19.
    Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR spektroskopiya v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Leningrad: Khimiya, 1983, p. 272.Google Scholar
  20. 20.
    Baranov, G.M. and Perekalin, V.V., Zh. Obshch. Khim., 1987, vol. 57, no.3, p. 793.Google Scholar
  21. 21.
    Botata, Zh.E., Deiko, L.I., Kostina, U.L., Baranov, G.M., and Berestovitskaya, V.M., Zh. Obshch. Khim., 1995, vol. 65, no.1, p. 160.Google Scholar
  22. 22.
    Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972. Translated under the title Sputnik khimika, Moscow: Mir, 1976, p. 387.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • N. A. Anisimova
    • 1
  • A. A. Kuzhaeva
    • 1
  • G. A. Berkova
    • 1
  • L. I. Deiko
    • 1
  • V. M. Berestovitskaya
    • 1
  1. 1.Gertsen Russian State Pedagogical UniversitySt. PetersburgRussia

Personalised recommendations